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We continue our series on Iran and its nuclear program now. President Obama has said he wants to see if diplomacy can keep Iran's nuclear ambitions in check. But this summer's disputed elections and a crackdown on opposition figures in Iran are complicating the administration's outreach.

NPR's Michele Kelemen reports.

MICHELE KELEMEN: Because the U.S. has no diplomatic relations with Tehran, it's hard to find U.S. officials who have actually negotiated with Iranians. John Limbert had his own unhappy experience. He was a political officer in Tehran 30 years ago, when students stormed the U.S. Embassy and took him and his colleagues hostage.

Mr. JOHN LIMBERT (Charge D'Affaires of the United States Embassy, Khartoum, Sudan): That's one of those days when you're not at the negotiating table because we were holding such a weak hand. And the people on the other side -that is, the students attacking the embassy - had no reason to negotiate.

KELEMEN: Now retired from the State Department, Limbert has written a book called "Negotiating with Iran: Wrestling the Ghosts of History." He says 30 years of trading slogans has not gotten either side anywhere. So when the Obama administration came in talking about engagement, he saw it as a good way to knock Tehran off balance. He says keep at it.

Mr. LIMBERT: Keep using the same tone. Tone is very important. It creates a dilemma because it's very difficult to maintain this image of hostility and enmity from the United States when the talk is of friendship and engagement and dealing as equals.

KELEMEN: However, with Iranian opposition figures facing what many describe as show trials, it's difficult for the Obama administration to keep its hand outstretched.

Dr. TRITA PARSI (President, National Iranian American Council): The timing of diplomacy is absolutely essential. And the time is not now.

KELEMEN: That's Trita Parsi of the National Iranian American Council. He favors diplomacy but is calling for a tactical pause.

Dr. PARSI: We have to take a pause and stand back and let there be greater political clarity on the Iranian side. Under these circumstances, in which the Ahmadinejad government and the system as a whole essentially lacks stability, lacks legitimacy internally, I don't believe the Iranians will be able to come to the table and actually negotiate.

KELEMEN: Parsi says the Obama administration won't want to do anything to hurt the chances of the opposition movement. But Hillary Mann Leverett, who was the director of Iran and Persian Gulf affairs at the National Security Council under President Bush, says the U.S. needs to forget about finding moderates in Tehran.

Ms. HILLARY MANN LEVERETT (Former Director of Iran and Persian Gulf Affairs, National Security Council): Our attempts to play that game in Iranian politics has always failed and has always backfired. And I think it's a mistake to do that again today.

KELEMEN: She is one of those rare former officials who has actually negotiated with Iranians about how to cooperate in Afghanistan and in dealing with al-Qaida.

Ms. LEVERETT: The Iranians I dealt with were authoritative, spoke for the government, even though they represented different ministries and different power centers within the government. They were able to deliver not everything that we asked for, but a lot of what we asked for. And so, this idea that Iran is either too divided or is even too depraved to negotiate with the United States is not something I experienced at all in the two years of negotiating with them.

KELEMEN: Leverett thinks the Obama administration is already setting itself up for failure by setting deadlines and talking about crippling sanctions, as Secretary of State Hillary Clinton has done.

Secretary HILLARY CLINTON (Department of State): We clearly see the threat that Iran poses, not only on its own and its attitude towards its neighbors, as well as, unfortunately, its own people, but the possibility, I would say probability, that Iran becoming a nuclear weapons state would kick off a nuclear arms race in the Middle East.

KELEMEN: She's trying to get China and others on board for tough sanctions. There is talk about cutting gasoline supplies to Iran. But analyst Trita Parsi thinks that could backfire, turning America into the boogeyman once again.

Dr. PARSI: The more you talk about what would happen after diplomacy if it fails, the more you talk about your Plan B, the more you undermine your Plan A.

KELEMEN: He's also worried that the U.S. is focusing solely on the nuclear issue. Hillary Mann Leverett says it's a fool's errand to try to deal with that issue in isolation when there are other concerns, such as Iran's influence in Iraq and Afghanistan, and its relations with militant groups.

Ms. LEVERETT: They will require security guarantees to constrain their nuclear program. We, the United States, cannot offer them security guarantees as long as they have a relationship with any of these groups, whether it's Hamas, Hezbollah, the Sadrists in Iraq. So it really has to be done as a package.

KELEMEN: She's calling for something akin to the Nixon era rapprochement with China. But others say the Obama administration will have to wait and see how the political situation in Iran plays out first.

Michele Kelemen, NPR News, Washington.

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